Biohydroxylations of Cbz-protected alkyl substituted piperidines by Beauveria bassiana ATCC 7159

S J Aitken, G Grogan, C S Y Chow, N J Turner, S L Flitsch

Research output: Contribution to journalArticlepeer-review

Abstract

N-Benzyloxycarbonyl (Cbz) protected piperidines are hydroxylated with greater regioselectivity than the corresponding N-benzoyl analogues when incubated with the fungus Beauveria bassiana ATCC 7159. Cbz-protected piperidines 1-3, 5-7, have been biotransformed by growing cell suspensions of this fungus to yield predominantly 4-hydroxylated products in up to 48% yield. The regiospecificity of hydroxylation was only compromised significantly with N-Cbz-3-methylpiperidine 3 and N-Cbz-2-methylpiperidine 4 where hydroxylation occurred in both the 3 and 4 positions.

Original languageEnglish
Pages (from-to)3365-3370
Number of pages6
JournalJournal of the Chemical Society-Perkin Transactions 1
Issue number20
Publication statusPublished - 21 Oct 1998

Keywords

  • MICROBIAL HYDROXYLATION
  • ENANTIOMERIC EXCESS
  • SULFURESCENS
  • 2-CYCLOALKYLBENZOXAZOLES
  • TRANSFORMATIONS
  • FUNGAL

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